(2R,4S,5S,7S)-7-(4-methoxy-3-(3-methoxypropoxy)benzyl)-5-amino-4-hydroxy-2,8-dimethyl-N-(4-(methylamino)-4-oxobutyl)nonanamide hydrochloride

ID: ALA537668

PubChem CID: 23626575

Max Phase: Preclinical

Molecular Formula: C28H50ClN3O6

Molecular Weight: 523.72

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CNC(=O)CCCNC(=O)[C@H](C)C[C@H](O)[C@@H](N)C[C@H](Cc1ccc(OC)c(OCCCOC)c1)C(C)C.Cl

Standard InChI:  InChI=1S/C28H49N3O6.ClH/c1-19(2)22(16-21-10-11-25(36-6)26(17-21)37-14-8-13-35-5)18-23(29)24(32)15-20(3)28(34)31-12-7-9-27(33)30-4;/h10-11,17,19-20,22-24,32H,7-9,12-16,18,29H2,1-6H3,(H,30,33)(H,31,34);1H/t20-,22+,23+,24+;/m1./s1

Standard InChI Key:  RVLFDKRINKJMPX-QFUPZHBKSA-N

Molfile:  

     RDKit          2D

 38 37  0  0  0  0  0  0  0  0999 V2000
    7.6894   -7.1383    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5972   -1.5031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5951   -3.0039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8933   -3.7570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8912   -5.2578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1894   -6.0109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2296   -5.4127    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1872   -7.5117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4854   -8.2648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4833   -9.7657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7815  -10.5188    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4430  -10.3638    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -9.0775  -12.7727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8509   -5.8560    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2956   -3.7547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2952   -4.9547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2564   -3.1547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5973   -1.5031    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5951   -3.0039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5257   -7.6667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5972    1.5031    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5955    2.7031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8933   -3.7570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8912   -5.2578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1894   -6.0109    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1877   -7.2109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0754  -14.2735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3736  -15.0266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3715  -16.5274    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  -11.4139  -14.4284    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -11.4095  -17.1295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  2  7  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  6
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  2  0
 17 19  1  0
 19 20  1  0
 11 21  1  6
  9 22  1  6
 22 23  1  0
 22 24  1  0
  2 25  1  0
 25 26  1  0
 15 27  1  6
  3 28  1  0
 28 29  1  0
 26 30  1  0
 30 31  1  0
 31 32  1  0
 32 33  1  0
 20 34  1  0
 34 35  1  0
 35 36  1  0
 35 37  2  0
 36 38  1  0
M  END

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 523.72

Molecular Weight (Monoisotopic): 523.3621

AlogP: 2.67

#Rotatable Bonds: 19

Polar Surface Area: 132.14

Molecular Species: BASE

HBA: 7

HBD: 4

#RO5 Violations: 1

HBA (Lipinski): 9

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 9.57

CX LogP: 1.81

CX LogD: -0.31

Aromatic Rings: 1

Heavy Atoms: 37

QED Weighted: 0.21

Np Likeness Score: 0.05

References

1. Göschke R, Stutz S, Rasetti V, Cohen NC, Rahuel J, Rigollier P, Baum HP, Forgiarini P, Schnell CR, Wagner T, Gruetter MG, Fuhrer W, Schilling W, Cumin F, Wood JM, Maibaum J..  (2007)  Novel 2,7-dialkyl-substituted 5(S)-amino-4(S)-hydroxy-8-phenyl-octanecarboxamide transition state peptidomimetics are potent and orally active inhibitors of human renin.,  50  (20): [PMID:17824679] [10.1021/jm070314y]

Source

Source(1):

• Scientific Literature